A crowded beach with people sunbathing and swimming.

Southwest Florida Honeymoon Vacations

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    Save up to CA $4,200 when you book a flight and hotel together*
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Top Honeymoon vacation packages in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
  • Dec 14 - Dec 18

    Marriott Sanibel Harbour Resort & Spa + Flight

    Punta Rassa
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,004 reviews)
    "I just received a $200 charge on my CC post stay for “Resort Fees” which include things I did not use. Additionally, the resort charges $25/day just to park at a place you already paid to stay at. My room was at the Captiva bldg which is not near the main building. The Captiva building does have a pool…but it was closed the ENTIRE time of my stay. I called for shuttles to the main building several times and was never picked up after waiting 30 minutes..The mail buildings pool does not look..."
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • Nonstop RSW - YYZ • Nonstop
    CA $1,304
    CA $1,021
    per traveller
    found 20 hours ago
    Marriott Sanibel Harbour Resort & Spa
  • Jan 17 - Jan 21

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    4 nights
    4.5 star property
    9.0/10 - Wonderful (1,000 reviews)
    "Great resort. Probably the nicest on the entire run of resorts on this beach. And that includes the Ritz-Carlton just upo the way. Obviously, the Ritz is classier, but La Playa felt more exclusive and comfortable. The beach experience is top-notch, with complimentary umbrellas and beach chairs upon request. The bar and restaurant were very good. Drinks are pricey, to be sure, which can add up if you're ordering while relaxing on the beach for days on end. About a 25 minute drive to the best..."
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • Nonstop RSW - YYZ • Nonstop
    CA $4,955
    CA $3,233
    per traveller
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • Feb 5 - Feb 9

    Tween Waters Island Resort & Spa + Flight

    Captiva
    4 nights
    3.0 star property
    8.8/10 - Excellent (1,000 reviews)
    "Very relaxing."
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • Nonstop RSW - YYZ • Nonstop
    CA $1,761
    CA $1,317
    per traveller
    found 1 day ago
    Tween Waters Island Resort & Spa
  • Feb 2 - Feb 6

    Naples Beach Club, A Four Seasons Resort + Flight

    Coquina Sands
    4 nights
    5.0 star property
    9.6/10 - Exceptional (48 reviews)
    Roundtrip • Toronto (YTO) - Fort Myers (RSW)
    YYZ - FLL • 1 stop FLL - YYZ • 1 stop
    CA $6,806
    CA $5,449
    per traveller
    found 1 day ago
    Naples Beach Club, A Four Seasons Resort
  • Feb 2 - Feb 6

    Signia Hilton Naples Grande Beach Resort + Flight

    Pelican Bay
    4 nights
    4.5 star property
    9.0/10 - Wonderful (1,821 reviews)
    Roundtrip • Toronto (YTO) - Fort Myers (RSW)
    YYZ - FLL • 1 stop FLL - YYZ • 1 stop
    CA $3,067
    CA $2,459
    per traveller
    found 1 day ago
    Signia Hilton Naples Grande Beach Resort

Discover the most popular places to visit in Southwest Florida

What to do in Southwest Florida

Top Honeymoon Southwest Florida Hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a Southwest Florida vacation package cost?

Less than you might think — from just CA $1,021, in fact! By bundling flights, hotels and car rentals into your own custom-built vacation package, your getaway to Southwest Florida is just a few clicks away.

How do I get a cheap travel package to Southwest Florida?

Browse and book everything in the one place with our Southwest Florida vacation packages. We have incredible bargains on flights, hotels and more that'll keep your pocket happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 properties worldwide to select from, you'll have the flexibility to mix and match all you want.

Where should I stay in Southwest Florida?

You can't go past Tampa, with terrific landmarks including Raymond James Stadium and University of South Florida to discover. Or, if sights like Edison and Ford Winter Estates and Sun Splash Water Park are more your scene, Fort Myers is the place for you.

What are the top hotels in Southwest Florida?

Naples Grande Beach Resort and La Quinta Inn & Suites by Wyndham Naples East (I-75) know how to make their guests feel welcome in Naples. If your itinerary also includes Cape Coral, take a look at Trianon Bonita Bay and Sanibel Island Beach Resort. Both are very popular with travelers.

How far in advance should I book my Southwest Florida vacation?

Get rewarded with the widest variety at the cheapest prices by booking your vacation to Southwest Florida nice and early. Air carriers generally advertise tickets around a year before departure, so reserve your spot as soon as possible. That being said, Expedia is dedicated to providing you with the best deals around, so there's never a bad time to book your dream vacation!

What does an Expedia Southwest Florida travel package include?

That mostly depends on you. You can select from a range of Southwest Florida bundles, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Southwest Florida vacation looks like, you're sure to save!

What should I know before booking a Southwest Florida travel package?

You can save a tidy sum by combining your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next awesome vacation is only a couple of clicks away.

Can I choose my airline with a Southwest Florida Expedia vacation package?

Yes — that's the beauty of an Expedia package. You're the boss! We have access to more than 550 partner airlines all over the world, so you have options galore when putting together your Southwest Florida escape.

If I'm not able to travel, can I cancel my Southwest Florida vacation package?

It's hard to predict what the future holds, so it's good to know that you can cancel or change your Southwest Florida vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.